Clad in a black hoody and jeans, the man straddles a stepladder, spray can poised, baseball cap tilted backwards. Tip-toeing forward I watch, mesmerised, as he makes fine, yet deft strokes – a black line here, a grey smudge there – the ghostly figure of an old man's face coming to life on the sides of a solitary water tank.

In the distance, dead tree trunks stand anchored to a dusty red earth, their gnarled branches clutching at a cobalt blue sky as Peregrine falcons wheel overhead. This is the Winton Wetlands, a restoration project on the outskirts of Benalla in rural Victoria, the least likely place to find some of the world's best street art.

"Every wall is a different size and has a different surface," says Brisbane-based street artist Guido van Helten, whose murals can be seen on silos in Brim in north-western Victoria, as well as on buildings across the Ukraine, Mexico, Poland, Belarus, Arctic Svalbard and Estonia. "I adapt and learn as I go."

Only in its second year, Guido's work is part of the Benalla Street Art Wall to Wall Festival, an event organised by Shaun Hossack of Melbourne studio Juddy Roller, a street artist who had grown up in the area and is now leading the charge to inject life back into the town. After two annual Wall to Wall festivals Benalla now has 29 murals, with 2017 set to be even bigger and better again.

The remarkable thing is that the festival has the complete backing of the council, Benalla art gallery and business community; even the locals are behind it, turning up in droves with their fold-up chairs and picnic rugs. "The artworks show kids growing up in rural communities that there are more things to look up to than sport," says Guido.

Back in Benalla, the small town is literally buzzing with the sound of air compressors, scissor lifts and spray cans as 14 paint-splattered artists – seven male and seven female – take up the challenge to complete their artworks over one weekend. "Gender equality was an inspiration for this event," says local MP Jaclyn Symes at the launch of the festival."Hopefully the festival will be a trigger for gender equality conversations."

I start on a back alley where Melbourne-based Adnate is sketching the outline of a pair of eyes. A famed portrait painter, whose signature murals of Indigenous Australians can be seen in Melbourne, Newcastle, Sydney and Townsville, Adnate is a one of the festival's drawcards, his portrait of a Burmese girl painted during the 2015 Wall to Wall named the eighth best mural in the world by street-art site Widewalls.

"One of the things I love about street art is that it's always changing," he says. "Layers and layers of paint and history have taught me that nothing lasts forever."

The fleeting nature of the works is a common dominator, with many of the artists admitting they started out doing graffiti art. "It's where you learn to paint fast," says Kaff-eine, as she applies tan paint to the back of the Benalla toilet block. "Putting a poignant art work in a pedestrian place like a toilet is unexpected."

Kaff-eine is a law graduate who quit her job, sold her house and has now been painting full-time for five years in places as diverse as the Philippines, New York, New Orleans and Germany. Her signature work is a deer-hunter character – not quite human, not quite animal. "They don't have race, age, gender or sexuality," she says.

The ambitious painting is popular (everyone heads to the loo at some point) attracting an eager crowd of onlookers, who stand about scratching their beards trying to work out what it is. Gradually the scene evolves – three figures, one alone and two caught in a struggle. "I don't know what the hell it means," says an old timer, shuffling by on his walking frame. "But I like it."

Another massive mural is under construction on the side of a Georgina's restaurant. At first it's just white lines, but over the course of the day the figure of a beautiful, tattooed woman resting against bed sheets comes to life beneath the hands of Smug, a painter originally from Jervis Bay, now living in Glasgow.

Other crowd favourites include Goodie's pensive portraits, Sirum's kelpi-cross dog on the side of a former telephone exchange and Dvate's Ned Kelly, paying homage to the local outlaw's bushranging days.

Mingling with the artists, watching them create their works, and momentarily slipping through a portal into a world that's normally shadowy or inaccessible is the real strength of this weekend. So too is watching a country community come together – from the Indian cafe getting a Mahatma Gandhi make-over to the children's paint-by-numbers community wall. There's yoga by the lake, stencil workshops, tea and chocolate tastings, and live music by local bands and DJs all day. It's Benalla's Big Day Out meets Archibald Prize, with a down-on the-farm twist.

Back at the wetlands the sun is setting as Guido steps back from his near-completed portrait; a man looking down, eyes closed and crinkled, a knowing smile at his lips. Rumour has it, it is a CFA volunteer firefighter, but in typical Guido form he's not saying, not yet anyway, preferring to let the work speak for itself. Over the coming days he will complete two more portraits on the water tank.

"I like to bring street art to places where it has never been seen before," he says, staring off into the vast spaces around him.

TRIP NOTES

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DRIVE + FLY

Benalla is around 1½ hours' drive from Albury Airport (or about 3½-hours' drive from Melbourne). QantasLink, Regional Express (Rex) and Virgin Australia all fly from Sydney and Melbourne to Albury. See qantas.com.au; rex.com.au; virginaustralia.com

STAY

Clement House B&B (25 Nunn St Benalla) is a large Victorian-era home on a quiet street near the centre of Benalla. For bookings and prices see clementhouse.com.au

SEE

The next Benalla Wall to Wall will be held from April 7-9, 2017. Grab a self-guided map or turn up to one of the free walking tours. See program for fringe events and attractions. See benallastreetart.com.au

Kerry van der Jagt was a guest of Tourism Victoria and Tourism North East.